US12150378B2ActiveUtilityPatentIndex 51
Luminescence device and polycyclic compound for luminescence device
Est. expiryOct 7, 2039(~13.3 yrs left)· nominal 20-yr term from priority
Inventors:JIN XIULAN
H10K 85/6576H10K 85/6574H10K 85/657H10K 50/15C07D 495/04C07D 491/048H10K 85/615H10K 85/631H10K 85/636H10K 85/6572H10K 85/633H10K 85/626C07B 2200/05C09K 2211/1029C09K 2211/1092C09K 2211/1088C09K 2211/1037C09K 2211/1033C09K 2211/1022C09K 2211/1014C09K 2211/1011C07B 59/002C09K 11/06
51
PatentIndex Score
0
Cited by
25
References
18
Claims
Abstract
The present disclosure herein relates to a luminescence device including a polycyclic compound represented by Formula 1 in at least one functional layer and achieving a low driving voltage, high efficiency, and long life, and a polycyclic compound represented by Formula 1 below.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A luminescence device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
at least one functional layer disposed between the first electrode and the second electrode,
wherein the at least one functional layer comprises a polycyclic compound represented by Formula 1:
wherein in Formula 1,
X is O, or S,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
Ar 1 and Ar 2 are each independently represented by Formula 2:
*—(Ar 11 ) p —Ar 12 Formula 2
wherein in Formula 2,
Ar 11 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group,
Ar 12 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
p is 0 or 1,
provided that i) when n is 1 and *—(Ar 11 ) p Ar 12 of Ar 1 is an unsubstituted biphenylene group, then *—(Ar 11 ) p Ar 12 of Ar 2 is not an unsubstituted dibenzothiophenylene group, and ii) when n is 1 and *—(Ar 11 ) p Ar 12 of Ar 2 is an unsubstituted biphenylene group, then *—(Ar 11 ) p Ar 12 of Ar 1 is not an unsubstituted dibenzothiophenylene group,
wherein in Formula 1,
Ar 3 is a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
L is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms,
l is an integer of 0 to 3,
m is an integer of 0 to 4, and
n is an integer of 0 to 3.
2. The luminescence device of claim 1 , wherein the at least one functional layer comprises:
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region; and
an electron transport region disposed on the emission layer,
wherein the hole transport region comprises the polycyclic compound.
3. The luminescence device of claim 2 , wherein the hole transport region comprises:
a hole injection layer disposed on the first electrode; and
a hole transport layer disposed between the hole injection layer and the emission layer,
wherein the hole transport layer comprises the polycyclic compound.
4. The luminescence device of claim 1 , wherein the polycyclic compound comprises one acyclic amine.
5. The luminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-1 or Formula 1-2:
wherein in Formula 1-1 and Formula 1-2,
Ar 21 , Ar 22 , Ar 31 , and Ar 32 are each independently represented by Formula 2,
Ar 23 and Ar 33 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
L 11 , and L 12 are each independently a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms, and
n11, and n12 are each independently an integer of 0 to 3.
6. The luminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-3:
wherein in Formula 1-3,
X, R 1 , R 2 , Ar 1 , Ar 2 , L, and I to n are the same as defined in Formula 1.
7. The luminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-4:
wherein in Formula 1-4,
n1 is 0 or 1, and
X, R 1 , R 2 , Ar 1 to Ar 3 , 1, and m are the same as defined in Formula 1.
8. The luminescence device of claim 1 , wherein Ar 1 and Ar 2 are each independently represented by Formulae 1-1 to 1-10:
wherein in Formulae 1-1 to 1-10,
R 11 to R 27 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
r1, r2, and r5 are each independently an integer of 0 to 4,
r3 is an integer of 0 to 5,
r4, r6, r8, and r10 to r12 are each independently an integer of 0 to 7,
r7 is an integer of 0 to 9,
r9 and r13 are each independently an integer of 0 to 8, and
q1 and q2 are each independently 0 or 1.
9. The luminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-5:
wherein in Formula 1-5,
n1 is 0 or 1, and
X, Ar 1 , and Ar 2 are the same as defined in Formula 1.
10. A luminescence device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
at least one functional layer disposed between the first electrode and the second electrode,
wherein the at least one functional layer comprises a polycyclic compound comprising at least one among Compound Group 1 and Compound Group 2:
11. A polycyclic compound represented by the following Formula 1:
in Formula 1,
X is O, or S,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
Ar 1 and Ar 2 are each independently represented by Formula 2:
*—(Ar 11 ) p —Ar 12 Formula 2
wherein in Formula 2,
Ar 11 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group,
Ar 12 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
p is 0 or 1,
provided that i) when n is 1 and *—(Ar 11 ) p Ar 12 of Ar 1 is an unsubstituted biphenylene group, then *—(Ar 11 ) p Ar 12 of Ar 2 is not an unsubstituted dibenzothiophenylene group, and ii) when n is 1 and *—(Ar 11 ) p Ar 12 of Ar 2 is an unsubstituted biphenylene group, then *—(Ar 11 ) p Ar 12 of Ar 1 is not an unsubstituted dibenzothiophenylene group,
wherein in Formula 1,
Ar 3 is a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
L is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms,
l is an integer of 0 to 3,
m is an integer of 0 to 4, and
n is an integer of 0 to 3.
12. The polycyclic compound of claim 11 , wherein the polycyclic compound comprises one acyclic amine.
13. The polycyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-1 or Formula 1-2:
in Formula 1-1 and Formula 1-2,
Ar 21 , Ar 22 , Ar 31 , and Ar 32 are each independently represented by Formula 2,
Ar 23 and Ar 33 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
L 11 , and L 12 are each independently a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms, and
n11, and n12 are each independently an integer of 0 to 3.
14. The polycyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-3:
wherein in Formula 1-3,
X, R 1 , R 2 , Ar 1 , Ar 2 , L, and I to n are the same as defined in Formula 1.
15. The polycyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-4:
wherein in Formula 1-4,
n1 is 0 or 1, and
X, R 1 , R 2 , Ar 1 to Ar 3 , 1, and m are the same as defined in Formula 1.
16. The polycyclic compound of claim 11 , wherein Ar 1 and Ar 2 are each independently represented by the following 1-1 to 1-10:
wherein in 1-1 to 1-10,
R 11 to R 27 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms,
r1, r2, and r5 are each independently an integer of 0 to 4,
r3 is an integer of 0 to 5,
r4, r6, r8, and r10 to r12 are each independently an integer of 0 to 7,
r7 is an integer of 0 to 9,
r9 and r13 are each independently an integer of 0 to 8, and
q1 and q2 are each independently 0 or 1.
17. The polycyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-5:
in Formula 1-5,
n1 is 0 or 1, and
X, Ar 1 , and Ar 2 are the same as defined in Formula 1.
18. A polycyclic compound selected from Compound Group 1 or Compound Group 2:Cited by (0)
No later patents cite this yet.
References (0)
No backward citations on record.